Clouded Judgement

JULY 2, 2025

The document contains a plethora of information on the company including a general overview, up to date financials, risk factors to the business, cap table highlights and much more. The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions.

Benchmarks 196

Benchmarks Data Software Review AI 196

BetterCloud

JULY 24, 2025

Yet, mastering SaaS management metrics is crucial for optimizing software ecosystems. These metrics provide insights into application performance, security , and cost-effectiveness. By focusing on the right metrics, IT leaders can streamline operations and enhance security protocols.

Metrics 52

Metrics Management SaaS compliance 52

Clouded Judgement

DECEMBER 20, 2024

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 144

Cloud Banking Payment Features Subscription 144

SaaStr

MAY 26, 2025

Strategic Guidance : AEs will become trusted advisors rather than information sources, as prospects will already have baseline knowledge from AI interactions. Develop New Performance Metrics : Traditional sales metrics don’t capture the effectiveness of this hybrid approach.

Scale 247

Scale Sales Hiring AI Sales 247

Clouded Judgement

JULY 4, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 157

Cloud Investment Payment Features Subscription 157

Clouded Judgement

JUNE 27, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 157

Cloud Sales Hiring Scale Investment 157

SaaStr

MARCH 12, 2025

“Marketing is fluffy and unmeasurable” – Unlike sales, which has clear metrics like quota attainment, founders often believe marketing can’t be measured. Instead, focus on two key metrics: Pipeline coverage – Do we have a chance to hit our numbers? Actual sales – Did we hit our targets?

Sales Hiring 202

Sales Hiring Marketing Technical Review Underperforming Technical Team 202

SaaStr

MARCH 9, 2025

Meeting intensity KPI challenge : Sometimes AI efficiencies can reduce a company’s core metrics (like Calendly’s “meeting intensity”), requiring leadership to make conscientious decisions about value tradeoffs. Building separate AI interfaces can create unnecessary tech debt and learning curves.

AI 202

AI Scale Education User Experience 202

SaaStr

JULY 11, 2025

This isn’t a vanity metric but a North Star that ensures they’re measuring actual value creation rather than superficial engagement. Monthly Active Users Can Mean Completed Designs, Not Just App Opens Canva defines “monthly active use” as completing a design—something shared, downloaded, saved, or published.

Scale 175

Scale AI Enterprise Venture Capital 175

Clouded Judgement

JUNE 6, 2025

ARR (annual recurring revenue) is a hallmark SaaS metric rooted in predictability. However, many companies misuse ARR and count forms of non-recurring revenue as ARR, confusing the metric. I created this subset to show companies where FCF is a relevant valuation metric. Commercial signals (e.g.,

Cloud 144

Cloud Technical Review Software Review Technical Advisors 144

User Pilot

OCTOBER 10, 2024

Once the user completes verification, they are guided through a short welcome survey that gathers critical information like the user’s role, goals, and company details. Now, this onboarding flow works well because Miro is a highly visual tool that doesn’t need much information to onboard users, nor has a long sales cycle.

Onboarding 105

Onboarding SaaS Software Communication 105

SaaStr

JULY 1, 2025

Cultural Shift Required : Stop measuring AEs on activity metrics (calls made, emails sent). Start measuring outcome metrics (pipeline quality, deal velocity, win rate). The math works: $200K AE salary + $50K AI tooling = $350K more revenue per rep. Let AI handle the activities. The sales AI explosion isn’t coming—it’s here.

Scale 219

Scale Software Review Sales Hiring AI 219

SaaStr

JUNE 26, 2025

Companies like Decagon and Intercom have proven AI can handle complex workflows autonomously. Duolingo didn’t gradually increase from 10% to 80% – they saw explosive growth once the AI agents demonstrated consistent performance.

AI 268

AI Sales Generative AI Pricing 268

How To Buy Saas

DECEMBER 20, 2024

For SaaS companies, accounting becomes one of the most crucial processes to understand their financial and overall business health, and then make informed decisions about future steps. They provide valuable data to monitor business performance, pinpoint key areas to improve your efficiency and strategies, and make more informed decisions.

Payment Services 52

Payment Services SaaS Payments Payment Solutions Payment Features 52

SaaStr

FEBRUARY 7, 2025

The ROI of AI Needs to Be Measurable Dialpad’s success comes from relentlessly focusing on customer value: Customer success metrics : One customer achieved 20% efficiency gains in workflow improvement Specific use cases : AI Recaps feature distills key information from calls in real-time Continuous measurement : Use telemetry and observability (..)

AI 262

AI Scale Government compliance 262

Clouded Judgement

MARCH 28, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

OCTOBER 30, 2024

And there’s a rough metric you can use to meter this: for each 10% of your company you sell roughly, you’re going to give up a board seat. The amount of information that actually is confidential is about 5% of what we think it is. Nobody has time anymore, but you don’t want them to control it.

Venture Capital 312

Venture Capital Software Review Investment Startup 312

User Pilot

OCTOBER 31, 2024

How to apply actionable metrics to different SaaS business stages. It tracks key metrics such as feature usage , user flows, and behavior patterns to explore user preferences and pain points. It tracks key metrics such as feature usage , user flows, and behavior patterns to explore user preferences and pain points.

Strategy 105

Strategy Underperforming Technical Team Government Customer Lifetime Value 105

Clouded Judgement

JULY 11, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 144

Cloud Marketing Scale AI 144

Clouded Judgement

JANUARY 24, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Enterprise 157

Enterprise AI Cloud Artificial Intelligence 157

Clouded Judgement

JUNE 13, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 144

Cloud Data AI Investment 144

SaaStr

FEBRUARY 25, 2025

Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts. This holistic perspective helps you position your company more effectively and make informed strategic decisions about product direction, go-to-market approaches, and resource allocation. Get out of the home office.

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

Buffer Resources

JULY 25, 2024

Your profile picture and headline will appear as the author’s information, so keep them updated and relevant. Monitor metrics like open rates, click-through rates, and engagement to understand what resonates with your audience and refine your content strategy accordingly. Can I monetize my LinkedIn newsletter?

Social Media 123

Social Media Engagement Metrics Strategy 123

Buffer Resources

AUGUST 7, 2024

  A lot of them are “done for you,” with application processes, teams, and technology sorting the most ideal partners for you.

Social Media 113

Social Media Compensation Technical Review Branding 113

Clouded Judgement

FEBRUARY 14, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 144

Cloud Software Payment Features Subscription 144

Clouded Judgement

JUNE 20, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 157

Cloud AI Headcount Pricing 157

Clouded Judgement

MARCH 21, 2025

Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric. This is for information purposes and should not be construed as an investment recommendation.

Cloud 188

Cloud Payment Features Subscription Pricing 188

Buffer Resources

JULY 22, 2024

  Track ad performance in real-time While Meta got rid of its full Facebook Analytics platform in 2021, it still has excellent resources for understanding ad performance, including reach, engagement, conversions, and more metrics. This data is updated in real-time so you can adjust your campaigns based on performance.

Payment Methods 116

Payment Methods AI Search Advertising Social Media 116

ChurnZero

NOVEMBER 26, 2024

A clear, detailed, and well-written customer success job description is essential to attract the right candidate while providing important information about the company, necessary qualifications and skills for the role , company culture, benefits and more. Familiarity with customer success frameworks, metrics, and best practices.

Technical Review 52

Technical Review Sales Recruiting Customer Success Sales Hiring 52

SaaStr

JULY 14, 2025

Real orchestration starts with intensive human training: 60+ days of continuous education after deployment—not for the AI, but for your humans Training humans to work with AI systems that don’t behave like any software they’ve used before Continuous adaptation as both AI capabilities and business needs evolve Not a one-time setup cost – (..)

AI 175

AI Scale Artificial Intelligence Technical Review 175

SaaStr

JULY 22, 2025

What This Means For Your Hiring Strategy If you’re a CEO or board member, this data should inform how you think about GTM hiring: 1. years, maybe don’t structure their entire comp plan around 3-year performance metrics. Hire for quick ramp time. Look for pattern recognition and immediate impact potential.

Part-Time CTO 209

Part-Time CTO CTO Sales Hiring CTO Hire 209

Buffer Resources

SEPTEMBER 5, 2024

Next, I fill my outline with research – data, statistics, expert quotes, examples – and other valuable information to support my argument or advice. This gives me some breathing room to gather the rest of the information I know I’ll need.  Draft Time to bring your article to life! 

AI Search 108

AI Search Social Media Systems Review Technical Review 108

Clouded Judgement

MAY 16, 2025

As you all know, one of my favorite metrics to look at is net new ARR added in a quarter. Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. I created this subset to show companies where FCF is a relevant valuation metric.

Trends 144

Trends Cloud Payment Features Subscription 144

Buffer Resources

OCTOBER 2, 2024

It should ideally contain everything from organic traffic to PPC competitor research to engagement metrics to help you do a wholesome analysis. You can filter for views per hour (VPH), publishing date, views, and performance metrics. It’s even more basic — offering only the crucial metrics for your competitor research.

Social Media 120

Social Media AI Search Benchmarks Software Review 120

SaaStr

MARCH 23, 2025

Founder-led sales provides invaluable dat a When founders sell the first $2-3M, they generate critical insights on customers, conversion rates, and retention that inform the GTM strategy. Be explicit about success metrics Define what success looks like beyond revenue targets to align expectations.

Sales Recruiting 242

Sales Recruiting Sales Hiring Scale AI 242

Unbounce

JANUARY 6, 2025

The primary use cases for landing page funnels are: Lead generation : Capturing email addresses and contact information. Educate your audience with valuable information on common pain points. At this stage, the goal is to nurture these leads by providing more detailed information and building a relationship with them.

Sales Funnel 111

Sales Funnel Payment Methods SaaS Payments Payment Services 111